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Process for the preparation of R)‐6‐hydroxy‐8‐{1‐hydroxy‐2‐[2‐(4‐methoxyphenyl)‐1,1‐ dimethylethylamino]ethyl}‐4H‐benzo[1,4]oxazin‐3‐one, or a salt thereof and intermediates and intermediates thereof.

Provided herein is a process for preparing (R)‐6‐hydroxy‐8‐{1‐hydroxy‐2‐[2‐(4‐ methoxyphenyl)‐1,1‐dimethylethylamino]ethyl}‐4H‐benzo[1,4]oxazin‐3‐one hydrochloride, referred herein as compound 1, having the following structure:

The process is described in the following scheme:

O

OH

O O

O

O OCH2Ph

O HCl

HN

O OCH2Ph

R

HN

(a)

+

HN

N

X

OMe

OMe

(2)

(3)

(4)

X=Cl, Br, I R

R=H, CH2Ar

(b)

O

OH

HCl

O

HN

(c)

O OCH2Ph

OH HCl

R

HN

HN

N

OMe

OMe

(1)

(5)

The starting material Compound (2) may be synthesized for example by the processes described in US2005/0267106 or US2011/0124859 (for X=Cl and X=Br respectively). The starting material Compound (3) can be prepared for example as described in US2011/0124859.

Compound (4) may be prepared by combining Compound (2) with compound (3) in solvents such as, but not limited to, methanol, ethanol, isopropanol, butanol, acetone, MEK, MIBK, THF, 2‐Me‐THF, MTBE, dioxane, anisole, ethylene glycol, propylene glycol, DME, CPME, methyl acetate, ethyl acetate, acetonitrile, toluene, DCM, heptane, DMF, DMSO, NMP, 1,3‐Dimethyl‐2‐imidazolidinone (NMI), acetic acid or a mixture of any of these solvents, possibly containing water, in the absence or presence of an organic or inorganic base such as, but not limited to, KOAc, K2CO3, NaHCO3, NaOH, K3PO4, NaOtBu, KOtBu, DBU, triethylamine, DIPEA, pyridine, and in the absence or presence of a iodide source such as KI or tetralkylammonium iodide. The obtained Compound (4) depicted as the HCl salt, can be isolated as such or as a different salt or as the free base.